tagFirst TimeMy First Time with a Man

My First Time with a Man


This is a true story of my first time with a man. I was 68 years old and had been using various objects to insert in my ass while masturbating. I started with household items, such as candles, brush handles, etc. as well as fingers. I then moved up to carrots, small zucchinis and cucumbers.

I learned that having something shoved up my ass made my orgasms much more intense and explosive.

Wanting to get more realistic, I graduated to vibrators and dildos, After much experimentation with longer and fatter things, I began to fantasize about what it would feel like to be fucked by a real cock.

I tried a number of dating sites before I stumbled on Craigslist. After reading a ton of man4man ads and not finding what I wanted, I decided to place my own ad. I requested married men or men in a male/female relationship who wanted to try anal, but their female partners wouldn't do it.

I was deluged with responses! I narrowed the replies down to married veterans with 8 plus inch cocks. I further weeded them out by letting them know I was an overweight, semi-disabled vet who could host in my own home and exchanged no face photos.

I met with 5 guys before deciding to go with the second one.

He was about 30, nice looking, had a beautiful 10 inch cock, was married (showed me his and his wife's drivers licenses) and seemed as nervous I was. I lead him back to the bedroom, where we both stripped.

I laid face down on the bed and pointed out the lube on my nightstand. He began caressing and stroking my body with one hand and his cock with the other. He was having a little trouble getting hard and asked me if I would suck him.

"Yes!" I said.

He rubbed the head of his uncut cock on my lips. I took him in my mouth and held his big member in one hand and fondled his balls with the other. As his cock began to expand in my warm, wet mouth, I pulled back his foreskin gently, exposing the slick cock head. I began swirling my tongue around it as he began fucking my mouth. Soon it was almost fully hard and pushing against the back of my throat. I pulled his cock out, gagging a little, and continued stroking as I licked and sucked on his huge balls, one at a time.

He was moaning with pleasure as he picked up the lube and squirted some in my ass crack. He rubbed the tip of his forefinger over my wrinkled clean butthole then pushed his finger in me until it was going all the way in as he finger-fucked my asshole. He worked a second then a third finger deep inside me as I moaned in delight.

"Oh, yes! Please fuck me!" I begged, taking his now massive cock from my mouth.

I spread my legs wide and reached back, pulling open my ass cheeks as he climbed on the bed and knelt between my legs. He rubbed the bulbous head of his magnificent cock on my butt crack. As he pushed, I felt the pop of my sphincter as the tip went inside me,

"Oh, god, baby! Yes, YES! Fuck my man-pussy good!" I yelled, pushing back against him as he fucked his cock deeper and deeper inside me! I clenched and released my asshole around him as he fucked faster and faster.

"Oh, shit!" he yelled, "I never thought it would feel so good! It's better than my wife's pussy!' he moaned as he fucked harder and deeper.

All of a sudden I felt him go so deep he pushed through my inner sphincter into my bowels1 My ass was spasming involuntarily, now as he buried his massive cock to the hilt in my ass with his balls rubbing against mine. He grabbed my shoulders and fucked harder and harder, grabbing my shoulders and pulling himself harder into me.

"Oh, fuck, yeah! I'm cumming, baby! I'm CUMMING!!" He shouted as his body stiffened on top of me and I could feel his cock throbbing and twitching as he shot jet after jet of his warm baby seed deep inside me!

Finally he climbed off of me and gave me his cock which I eagerly licked and sucked clean.

"Well, I learned one thing, today. I am your cum slut whenever you want me!"

"It will be often!" he laughed.

And it was. 3-4 times a week until he moved away due to work. Now, with Craigslist gone, I go without. This was my first try. Let me know what you think and feel free to PM we with your thoughts, ideas and suggestions.

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by Anonymous

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by bigguy25109/05/18

one of my favorite fantasies

I liked your story and keep writing more in this vein.

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